51799-45-2

Upstream product

• 1016-09-7 benzhydryl methyl ether 
• 123-38-6 propionaldehyde 
• 95-14-7 1,2,3-Benzotriazole 
• 91-01-0 1,1-Diphenylmethanol 
• 121193-26-8 6'-benzhydryl-spiro[cholestan-3,2'-[1,3]oxathiane] 
• 71-43-2 benzene 
• 78-93-3 butanone 
• 97-93-8 triethylaluminum 
• 1439-07-2 trans-Stilbene oxide 
• 73006-65-2 1-(diphenylmethyl)-1H-1,2,3-benzotriazole 
• 6336-52-3 1,1-diphenylbutan-2-one 

Downstream Products

• 88639-80-9 2-Hydroxy-6-methyl-3-<1-(diphenylmethyl)-propyl>-4H-pyran-4-on 
• 41997-48-2 S-(-)-1,1-Diphenyl-butan-2-ol 
• 52199-79-8 Phthalic acid mono-((S)-1-benzhydryl-propyl) ester 
• 52248-55-2 Phthalic acid mono-(1-benzhydryl-propyl) ester 

Relevant academic research and scientific papers

Lewis base-catalyzed addition of trialkylaluminum compounds to epoxides

A novel concept for catalytic epoxide alkylation has been developed. Lewis bases like phosphanes, arsanes, stibanes, and sulfides were found to catalyze the alkylation of symmetrical epoxides with trialkylaluminum compounds very effectively at a 5 mol % level. Cyclic as well as acyclic epoxides were readily alkylated in good yields. In reactions with terminal epoxides a significant enhancement of rate and/or regioselectivity was noted in the Lewis base-catalyzed process. Coordination of the Lewis base to the Lewis acidic aluminum reagent was proved by 27Al and 31p NMR spectroscopy and is proposed to form a more nucleophilic alkylating agent.

Transformations of N-Substituted Benzotriazoles into the Corresponding Carbanions by C-Benzotriazole Bond Scission

Various TV-substituted benzotriazoles are transformed, by scission of the C-benzotriazole bond, into the corresponding carbanions by treatment with lithium. Thus, N-(diphenylmethyl)benzotriazole (1), N-benzylbenzotriazole (6), and N-allylbenzotriazole (10) all gave carbanions that reacted with diverse electrophiles to afford the corresponding products in good yields. This new methodology was successfully utilized to convert N-benzylbenzotriazole (6) and N-allylbenzotriazole (10) into dianion synthons by a sequential lithiation and reductive coupling and bis(benzotriazolyl)toluene (18) by double reductive couplings, demonstrating the synthetic potential of the present methodology.

Reductive electrophilic substitution of diarylmethyl methyl ethers: Synthetic applications

The reductive cleavage of diarylmethyl methyl ethers with Li metal in THF led to quantitative formation of the corresponding diarylmethyl anions. Quenching with electrophiles afforded substituted diarylmethanes in good to excellent yields.